During cold weather/temperature activities, headwear is typically utilized to warm the ears, neck and head. During these activities, people often listen to music, podcasts, or make phone calls through the use of earbud headphones connected by wire to a mobile device. During movement or athletic activities, however, earbuds are more likely to shift and slip within the ear, and may even be accidentally pulled from the ear, which can be aggravating, or even dangerous, to the wearer. In addition, it is uncomfortable for people to wear earbuds while also wearing headwear that cover their ears because the earbuds extend outwardly from the ears of the wearer and the headwear presses the earbuds further into the ear of the wearer, which creates an unwanted pressure in the ears of the wearer. The earbuds may also prevent the headwear from resting comfortably against the ears and/or the sides of the head of the wearer, which then allows cold air to enter the interior of the headwear. Thus, it would be desirable to provide an article of headwear having the ability to keep earbuds comfortably in place without the need for frequent adjustment and readjustment that also keeps the head, neck, and ears of a wearer warm.